May 19 - 26, 2018 & May 26 - June 2, 2018

Under the Tuscan Sun – The 10th Anniversary Celebration at a Special Time of Year!

TuscanyFeaturing Jim Cuddy (Canadian multi-Juno award winner and Canadian Music Hall of Fame and Order of Canada recipient) with special guests, Barney Bentall, Anne Lindsay, Colin Cripps, Dustin Bentall, Devin Cuddy and Sam Polley, and a special appearance by Queen’s Diamond Jubilee and Order of Canada Recipient, Tom Cochrane! In addition, featuring Olympians, Curt Harnett (multi-medalist and Chef de Mission for the Rio Olympic Games) and Melissa Tancredi (Double Olympic Bronze Medalist in soccer)!

La Dolce Vita! Tuscany is one of Italy’s best-loved regions in the world and home of the famous wines of Chianti and Montalcino! It combines a beautiful countryside reminiscent of the landscapes of Renaissance masterpieces, a rich artistic heritage including exquisite art and architecture, a glorious history, world renowned wines and delicious food. You will spend seven nights in the newly renovated, exquisite five-star Relais & Chateau Borgo San Felice and Winery, once a small eighth century hamlet located in the heart of the Siena countryside and the Chianti region. Set between Florence and Siena, San Felice, winner of numerous wine awards, is also the birthplace of the Super Tuscan and has been awarded “Most Excellent Hotel” on the Gold List by Condé Nast Johansens and rated in the Top 25 Resorts by Condé Nast Traveler.

A truly unique experience. What sets this trip apart is the music and getting to know the Olympians. We thought this was a once in a lifetime trip, but after such a fantastic experience, we know we will be back again soon.


TuscanyIn Tuscany, every picturesque town and village offers unique characteristics, charm and fantastic regional cuisine. It is known for its splendid landscapes with charming low hills lined with majestic olive groves, ancient vineyards, woods, isolated cypress trees and beautiful old farmhouses; all part of a landscape that seems to have been carefully tended since the dawn of time. Imagine cycling on the beautiful country roads of Chianti, stopping for a cappuccino in a quaint piazza, led by Italian guides and alongside some of Canada’s most revered Olympians and musicians. It is considered some of the best cycling in the world! Or imagine hiking through these ancient vineyards, also led by local Italian guides, and enjoying wine tastings, museum visits and wonderful lunches in quaint little Tuscan villages.

When you combine Tuscany with Gold Medal Plates it becomes more than magical! Some of the highlights will include a fantastic wine tasting by serious wine enthusiast Jim Cuddy and a spectacular visit to Castello di Fonterutoli, where you can choose to cycle or hike to the winery for a beautiful afternoon. There you will enjoy a traditional Tuscan lunch, great wines and hear amazing stories from Curt Harnett (Chef de Mission for the Rio Games and a Silver and Double Bronze Medalist in track cycling) and Melissa Tancredi (Olympic Double Bronze Medalist in Soccer) about their Rio Olympic journey. You will laugh, cry and be inspired by these amazing athletes who put it all on the line to represent our country!

Great people, a great destination and a memorable experience! This trip met and exceeded our expectations. We will definitely go on another GMP trip.


Tuscany CyclistsThere will be unplugged performances around the bar by Jim, Barney, Anne, Colin, Devin and Sam, and a special appearance by Tom Cochrane. As well, there will be an opportunity to take a coach or enjoy an epic cycle to Borgo’s world-class award winning Montalcino winery, 75 km from Borgo San Felice. There you will enjoy a traditional Tuscan picnic and Brunello wines. And if that isn’t enough, the week will culminate with a once-in-a-lifetime private GMP concert under the Tuscan stars with multi-Juno award winner and Order of Canada recipient Jim Cuddy and special guests, Juno award winner Barney Bentall, fantastic fiddler Anne Lindsay, amazing guitarist Colin Cripps, Juno nominated Devin Cuddy, Sam Polley and Jim’s boys – musicians in their own right.

It promises to be an unforgettable retreat under the Tuscan sky. Life just can’t get any sweeter than this in one of the most prized locations on the planet. Don’t miss this 10th anniversary…it will be unforgettable!


  • Accommodations, including gourmet breakfast, at the five-star Relais & Chateau Borgo San Felice, a small hamlet dating back to the Middle Ages converted to a magical oasis. The property boasts a large heated pool, state-of-the-art wellness centre and spa, tennis court, 24-hour concierge and the Poggio Rosso and Osteria del Grigio restaurants. The former, a winner of international awards, offers traditional
    Tuscan dishes imaginatively revisited and accurately prepared using locally sourced ingredients and a carefully-researched wine list that boasts 200 select labels
  • Welcome reception featuring exquisite wines from the San Felice cellar that houses 20 different labels, with a range of both red and white wines. The traditional Chianti Classicos, including the vigorous Riserva wines, are accompanied by other prestigious reds such as Campogiovanni, Brunello di Montalcino DOCG and Vigorello
  • Private GMP concert under the stars with all of the musicians
  • A fantastic wine tasting by wine enthusiast Jim Cuddy – not to be missed!
  • Cycling, hiking, wine tastings and evenings around the bar with your guest
    Olympians: Curt Harnett and Melissa Tancredi!
  • Cycling led by local guides on some of Tuscany’s best cycling routes (bike rental not included)
  • A traditional Tuscan picnic at Montalcino winery. You can choose to ride to the winery led by our local Italian guides or be taken by coach and enjoy time to explore the classic fairy-tale hilltop town of Montalcino – known as the City of Brunello!
  • A spectacular wine tasting at Castello di Fonterutoli and traditional Tuscan lunch in the Tuscan hills! The afternoon will feature amazing stories from Curt Harnett and Melissa Tancredi about their Rio Olympic journey. You can choose to ride or hike to the winery or go shopping on your way!
  • Take part as a player or spectator in the 4th annual Canada vs. Italy soccer match
    and defend Canada’s title!

Optional add-ons (at additional cost):

  • Rental of bike – there will be local guides for some of the best routes in the world
  • Guided hikes and wine tastings, including a hike and wine tasting to our Canadian friend’s winery set in the Tuscan hills, Tolaini Winery, and museum visits led by local guides
  • Hands-on Tuscan cooking class
  • Horseback riding in the heart of Tuscany
  • Hot air balloon ride to view Tuscany from extraordinary vantage points

Jim CuddyBarney BentallTom CochraneAnne LindsayDustin BentallDevin CuddyColin CrippsSam PolleyCurt Harnett Melissa Tancredi

Photos From Past Years

Tuscany Video 2017

Trips Promo Video